


Infiltration

by ImoutoCommissions



Series: Andrea's Boys [1]
Category: Original Work
Genre: Anal Sex, Blow Jobs, Crossdressing, F/M, Hand Jobs, Implied Pregnancy, Loss of Virginity, Multi, Omorashi, Painful Sex, Underage Sex, Vaginal Sex, commission
Language: English
Status: Completed
Published: 2020-07-14
Updated: 2020-07-20
Packaged: 2021-03-05 03:14:49
Rating: Explicit
Warnings: Underage
Chapters: 4
Words: 4,576
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25267450
Author URL: https://archiveofourown.org/users/ImoutoCommissions/pseuds/ImoutoCommissions
Summary: Andrea is tired of being denied access to the neighborhood boys' tree house, so she disguises herself as a boy, only to have her ruse exposed on the first day due to her full bladder. However, the boys are willing to keep her around, on a few conditions...
Series: Andrea's Boys [1]
Series URL: https://archiveofourown.org/series/2003203
Comments: 3
Kudos: 51





	1. Chapter 1

Andrea has had it with the boys in her neighborhood. She had been excited to be able to play in the cool tree house that the boys all play in, but when she first asked if she could play with them, all three of them turned her down, telling her that a cootie-infested girl like her is definitely not allowed in their tree house. Within an hour, they had a sign hanging up, specifically saying, “No Girls Allowed,” put in place just to remind her that she does not have any place there.

Though she is frustrated by it, she is not going to let this deter her. There are not many other play options in the neighborhood, and the tree house seems so cool when looking up from the ground, so she decides that she has to get in there, no matter what. It does not take her long to figure out a plan, and within a few days, she is ready to execute it.

She has never been particularly girly, so most of her t-shirts are not very feminine, and when she pairs them with her longer shorts and puts her long hair in a braid (her parents refuse to let her get a short cut, even though she thinks it would be easier to play with) to tuck under a cap, she thinks she passes pretty well for a boy. Andrew will be her new name, something pretty easy to keep track of due to the similarity to her actual name, and with that, she sets off to pose as the new boy in the neighborhood.

At first, she worries that they might not fall for it, but they seem to completely buy it. They welcome Andrew to the neighborhood, not seeming to recognize her face or the similarity in names, though they do say that Andrew will only be able to play with him if he can pass the tests to join their club. This is the part that she was waiting for, long before she was ever told that girls were not allowed.

She can gather as many worms as they want without being grossed out, climb tall trees without any fear, and keep up with them in any of their games. By the time they have finished hazing her, they are satisfied and grant the “new boy” entrance, and she feels very proud of herself for managing to fool the three of them. Finally, she is allowed to join their club and play in the tree house with them, which is getting off to a great start.

Until one of the boys, Trevor, pees out the window. Once she has gotten over being flustered over how suddenly he whips it out and does that, she realizes that she has to pee herself, since she has been out for a while, and the group has drank a bit to keep hydrated during the hot summer afternoon. There is no bathroom in the tree house, a problem that they obviously solve by just aiming out the window, but that is not something that Andrea can do, or else they will figure out right away that Andrew doesn’t exist.

If she were to even attempt it, they would easily be able to see the physical differences, and she would make a mess of herself in the process. However, she also knows that they would tease her for wanting to go inside to use the bathroom, since none of them have any issue doing it like this. Her only option, to keep her secret, is to keep holding it until it is time to go home for dinner. But that is easier said than done, especially with the boys not have any trouble with relieving themselves right in front of them.

Trevor is not the first, and Riley and Evan soon follow suit, while Andrea tries to ignore the way the sight and sound of it adds to the torture that her bladder is currently dealing with. She definitely should have been more careful about what she had to drink, definitely should have thought about her ruse a bit more carefully. Somehow, it just never occurred to her that she would not be able to go inside to use the bathroom. In the future, she can be a lot more careful, but for right now, she has to deal with the fact that she feels like she could burst at any moment, and that she keeps springing small leaks, that she hopes are not showing on her shorts just yet.

Time seems to drag on, and she can’t enjoy being able to hang out with them when her bladder is aching like this. There is no stopping the short spurts of pee that escape, and when a small wet patch forms on the front of her shorts, she hopes that she will be able to pass it off as sweat. But she can’t pass it off as sweat forever, especially as it continues to grow, and as her control continues to falter, until suddenly, she lets out a yelp of surprise, causing the other boys to look at her just as the floodgates burst open.

And so they have a full view of her soaking through her shorts, the wet spot expanding and expanding until she is peeing full force, creating a puddle on the floor of the tree house, some of it leaking through the cracks in the wood, no doubt sprinkling down below. No matter how she tries, she can’t stop it, until her bladder is empty and she is collapsing to her knees in tears, sobbing as she realizes that she has not only completely humiliated herself, but that she has also blown her big chance on day one.

The boy step closer to her, but instead of ridiculing her, they meet her with a sympathy that surprises her. Riley says, “You don’t need to cry, it’s not the first time it’s happened. I used to be too shy to pee in front of everyone else too, and I had an accident back then.”

“Right, we even have spare shorts up here, just in case!” Trevor adds. “So you can just get changed, I’m sure they’ll fit you!”

Andrea realizes that her cover has at least not been blown, and that the boys still think that she is a boy, like them. Shaking her head, she says, “No, I don’t want to take your clothes. I’ll be fine.” Really, she just doesn’t want to change in front of them, because she risks giving herself away, even if she tries to face the other direction.

“You’re going to get a rash if you don’t change,” Even protests, and the others agree with him. No matter how she tries to argue, the three of them will hear nothing of it, until they all ambush her at once, ready to force her to change, not understanding why “Andrew” is fighting this so hard.

“No! No, stop!” she cries, briefly forgetting her slightly deeper voice, becoming shrill as they pull down her shorts, only to discover her plain panties, not particularly girly, but definitely not suiting a boy either. With all of these factors in place, the jig is already up, but that is still not enough to stop them from yanking her panties down, to expose the ruse for good.


	2. Chapter 2

To Andrea’s great humiliation, her panties are pulled down, exposing her privates to the boys, and not only giving away her secret, but also showing them something she knows that she is not supposed to show them. The boys, growing angry as they realize that they have been duped, step back and let her kneel in the puddle she has made, Trevor yanking her hat off to let her braid fall. All three of them are not sure what to make of the heat between their legs, getting their first ever erections from the sight of a half-naked girl.

“Andrea!” he cries. “I should have known.”

“You tricked us!” says Even. “We said no girls allowed!”

“I’m sorry!” she sobs. “I just wanted to play with you, I-I…please, let me stay! We had fun before…before!”

The boys decide to discuss it amongst themselves, not letting her listen to their conversation as they speak in hushed whispers, remembering how she impressed them when they thought she was Andrew, and bringing up the potential merits of having a girl around. Soon enough, they have reached a decision, turning back to her to deliver their verdict.

“We’ve decided that you can stay,” Riley says, as the other two nod. Upon seeing her brighten up at his words, he continues, “But there are conditions!”

“We’re going to let you have a bucket to pee in,” Trevor adds. “But you have to let us watch you every time that you use it.”

“And you have to be our girlfriend! All three of us!” Evan finishes. “That means that you have to do everything a girlfriend does!”

Andrea is still so elated to even be allowed to stay after her true identity was revealed that she is quick to agree without actually thinking about it, saying, “Yes! Just as long as I can stay, I’ll do all of that!”

With that out of the way, she decides that she needs to head home now so she can properly get cleaned up, but they agree that she can come over tomorrow, and that they will start on her new role in their club then.

~X~

The boys convince her that she has to wear a real “girlfriend” outfit, instead of dressing up like Andrew from that point on, and her parents are surprised to see her leaving the house in a skirt and tank top more often lately. Whenever she is in the tree house, she has to do the things that they have decided a girlfriend does, such as serving as what she assumes must be a diligent housewife, serving them drinks and snacks, and going inside the house to restock whenever they run out. Sometimes, if she is bent over, they will swat at her butt.

Not only that, but every time one of the boys takes a drink, she has to take a drink as well, so that they know for sure she will be using the bucket regularly, giving them the chance to watch her while she pees again. Though she is not fond of being treated as basically a servant, she does like the attention that she gets when a boy will occasionally pull her onto his lap, pushing a hand up her shirt to fondle her flat chest, or a hand under her skirt to rub her thighs. Truthfully, she even likes how they look at her when she squats over the bucket to pee.

One afternoon, however, they decide to heat things up a little, making her drink double what they normally do, in between clamoring for her attention, with Andrea being pulled from lap to lap as they grope and tease her, ignoring the way she squirms with her bursting bladder. Though she protests often, it is not until she knows that she on the verge of soaking her panties that they finally let go of her to let her pee.

She very nearly loses control just trying to get to the bucket, and it is not a moment to soon, a massive burst of liquid escaping just as soon as she has her panties out of the way, squatting over the bucket. It is not a particularly large bucket, but the fact that she nearly completely fills it is still an impressive feat, and when she looks up at the boys, they have their cocks out of their shorts, stroking themselves, finding the sight too much to resist.

Andrea, after being played with so much while trying to avoid wetting herself, is now incredibly worked up, and she can’t help herself either, reaching out her hands to wrap around Trevor and Evan’s cocks, pushing their hands out of the way so that she can try jerking them off, her very first time doing something like this. While she pays attention to the two of them, Riley decides to take advantage of the way her mouth hangs open, slack-jawed from her surprise at discovering the three of them jacking off, to get his first ever blowjob, which is also the first that Andrea has ever given.

Things escalate between the four of them very quickly on that day, all of the sexual tension that his been building since the first time they saw her girlhood finally coming to a head. It is easy for Andrea to forget all of the annoying work that comes with being allowed to play inside the tree house when they are playing like this, working her hands up and down as she saw the two of them doing, with Riley jerking his hips into her mouth while she sucks, not sure what to do, but eager to do it.

Had he asked her to suck his cock ahead of time, she probably would have responded with disgust, but when it is forced upon her, she quickly discovers how much she actually likes it, how much she likes all of this. And with all three boys moaning pathetically for her, she loves the way that it makes her feel, knowing that this is all because of her. Trevor is the first to come, though he has no idea what is happening, what the overwhelming spasms of pleasure are.

All that he knows is that he is suddenly satisfied, experiencing his first dry orgasm. The other two boys want this for themselves, with Riley jerking his hips a bit faster into Andrea’s mouth, and Evan urging her to move faster. She doesn’t know what’s going on anymore than they do, but she is eager to help them reach that peak as well, eager to listen to their moans as they experience what Trevor has.

With one last, weak thrust, Riley is overcome, moaning and understanding immediately why Trevor reacted the way that he did. As he pulls out of her mouth, Evan comes as well, finishing with another pathetic moan, all three of them dazed and satisfied. Needless to say, this quickly becomes a regular part of their afternoon activities.


	3. Chapter 3

About a week after that incident, Evan dares Andrea to take her panties off completely after the first time they watch her pee in the bucket that day. Specifically, he says, “I bet you’d be too chicken to leave your panties off even if I dared you!”

Andrea, not wanting to back down from a challenge, is quick to say, “That’s what you think!” before discarding them, much to the interest of the boys. She will still be covered by her skirt, but they all know that it will not offer that much cover for her, and when she does her rounds, bringing them drinks and snacks, they get a lot bolder with their hands, reaching up higher so that they can fondle her hips and her bare butt. Normally, they would stop at the leg holes of her panties, but without the panties to give that guideline, it becomes easier for them to give into temptation.

This leaves Andrea even more flustered than usual, and it seems as though the room gets hotter and hotter every time one of them touches her, though she is fairly certain that has nothing to do with the summer heat. Eventually, Trevor gets bold enough to unzip his shorts while asking her to bend over and pick something up for him. With her girlhood revealed to him by the way her skirt peaks up, he can no longer resist the temptation to grab her and pull her onto his lap, his small cock pushing into her much tighter pussy.

None of them know much about matters of sex, and the sudden stabbing pain as her cherry is popped makes Andrea think that something is seriously wrong, and she screams out in agony, terrified that this might even be endangering her life, but Trevor does not seem to notice at all, too overwhelmed by the pleasure of being buried inside of her tight cunny. At the same time, Riley and Evan are fascinated by the sight, watching the way their friend’s cock disappears inside of her, going in and out, and so, they are oblivious to her pain as well. Even when he spreads her legs to give them a better view, and they get a glimpse of the blood seeping out of her, they are more interested in watching her lose her virginity.

All Andrea can do is hold on until the pain begins to fade. However, once it does start to fade, she starts to realize how nice it actually feels, having Trevor jerking his cock in and out of her, and soon enough, her worries have all but gone away completely. Now that it does not hurt so much, she is not as afraid of what is happening to her, and she begins moaning along with Trevor, until finally, he reaches his climax, thrusting up into her one last time as he comes. This time, it is a little different than what they are used to, a spurt of liquid shooting inside of her before he finally pulls out of her, with Andrea collapsing onto the floor below.

However, he is too dazed to notice, and the other boys are too eager for their own turns to notice it either. That is when Riley grabs hold of her, pulling her onto his cock, not giving her sore, deflowered pussy a chance to recover, and Evan, impatient, takes her mouth, so any protests that she may have had are quickly muffled.

Riley mimics what he just watched Trevor do to her, immediately overwhelmed by how good it feels, while Evan enjoys her mouth like he has grown used to over the past week. Riley does not take much longer than Trevor to reach his climax, though, the pleasure overtaking him from the start. He can definitely see why it was so exciting for Trevor, envious that he did not think of this sooner, though he does not mind that just as long as he gets to have his fun with her now.

Much like with Trevor, when he comes, it is different, and he is still so lost in his excitement that he does not notice the spurt of sticky, white fluid inside of Andrea, not even when he pulls out so that he can give Evan a turn with her. All the while, Evan has been doing his best not to give into pleasure before he had a turn in her cunt, which is easier said than done, because once she got over the shock of having him take her mouth without warning, she quickly got into the routine of sucking him off, something that she has learned rather well after the incident last week.

But Evan manages to hold out so that he is able to put Andrea on her back to have his way with her. While he is on top of her, he is overcome with the same bliss that the other boys have experienced, so glad that he was able to hold off long enough to be able to do this. He can perfectly understand the hype once he is buried inside of her, fucking her hard and fast and frantic, unable to control himself after working himself up so much while fucking her mouth. And Andrea is helpless beneath him, moaning as she lets the third boy have his way with her, too lost in it all to even be able to think anymore. Certainly too lost in it to realize that when he comes, he also fills her with a sticky substance, just the same as the other two boys.

They are much too exhausted from all that they have done to do anything else until it is time for her to clean herself up and head home, without another word.

~X~

The next day, the first thing that Andrea says is, “I had fun yesterday, but that was way too much! I’m still sore from how rough you guys were with me. So, we’re definitely not doing that today, and if you even try, I’m going to stomp your little balls! You need to give me time to recover, and if you’re ever that rough with me again, that threat goes double!”

Though the boys regret nothing of their previous day, they know that Andrea means business, and that it is not something that they will ever repeat. Still, that hardly seems to matter, just as long as they keep getting to do stuff with her, and as long as they are still able to feel that good.


	4. Chapter 4

Of course, once Andrea does recover from the soreness of losing her virginity, she is willing to let them have sex with her again, and it becomes a very regular part of their routine, with all four of them absolutely loving it. Somehow, they manage to continue not to notice that the boys have finally begun to properly ejaculate, both due to their general cluelessness about most things, due to not to being observant while distracted by fucking her, and due to always finishing while balls deep inside of her, most of the evidence ending up left behind by the time that they pull out.

Summer continues to pass by in a sweaty and lust filled daze, the things that happen within the tree house having almost a surreal and magical quality to them, in the way that only games between children can. But summer is passes by far too quickly, and with school on the horizon, the four of them know that the spell is going to have to be lifted sooner or later. And so, on the last day of summer, Andrea decides to make things a little bit special.

When she shows up in a sun dress, they are already excited, but even more so when she quickly sheds it to reveal the bikini she is wearing beneath. Initially, she had not been interested in it when her parents bought it for her, but now, she realizes she has gone all summer without showing it off, and the boys make her much more eager to show off. Needless to say, they all like her bikini quite a bit, jaws practically hitting the floor to see her in it. It is almost hard to remember how this all started, with her dressed as a boy to infiltrate their secret base, or that even before that, she was often seen dressed rather boyishly.

Though Andrea will probably never consider herself all that girly, she finds that she certainly does not mind showing off her feminine charms a little bit more, when it comes to the attention that she gets from the three boys that she has spent her summer with. At first, they start off with just some heavy petting, pulling her into their laps like usual, so that they can fondle her above the swim wear, and then a little bit below the swim wear as well, getting bolder and more excited as time goes on. Andrea is soon so excited that she finds herself getting onto Evan’s lap, pulling her bottoms aside so that she can sink down on his already exposed cock.

Right away, she starts bouncing on top of him, riding him while the other two boys starting jerking themselves off while they watch them go. And while Evan relaxes, letting her do whatever she wants on top of him, he rolls her bikini bottoms down so that he can expose her butt, groping and fondling it. Eventually, with a hand on each cheek, he begins pulling them apart, exposing the still virgin hole to the other two boys, which only gives them ideas.

“I bet I could slide my thing there,” says Trevor. “So if you took her mouth, then all three of us could share her at once.” Riley is game for this, but Andrea is a bit hesitant, remembering the last time they did something completely new.

“You have to be gentle with me,” she finally says, as she relents. “You remember what I said I’d do to you if you were rough with me, right?”

Remembering her threat, Trevor gulps before agreeing to take it slow, and not hurt her too bad. Getting into position behind her, he makes sure that he takes it slow as he fits his small cock inside of the even tighter hole. Even going slowly, there is still some pain and some time that it takes for her to adjust to having him inside of her. Despite his impatience, he manages to keep things at a pace that is not too much for Andrea to handle, in order to protect himself from her wrath.

But once he has fit himself inside of her completely, he can finally relax, and begin to thrust into her, causing her to cry out, the double stimulation already overwhelming her. He only adds onto it by reaching to pinch her nipples through the fabric of her swimsuit, but her moans are quickly muffled by Riley finally claiming her mouth, all three boys buried inside of her in some way, overwhelming Andrea completely as they all have their way with her.

Soon enough, each one comes in turn, but they are not ready to stop at that, switching off so that Riley gets her pussy, Evan gets her ass, and Trevor gets her mouth, keeping at that until they come again. Then, of course, they switch off one last time, each one exhausted but still up for a little more, so that they can get their last turn using one of Andrea’s holes. All the while, Andrea has come over and over again, losing count as the boys have their fun with her, leaving her a dazed and horny mess.

But eventually, the fun has to come to an end, and they all take their time to rest, before breathlessly agreeing that this was a good way to end their summer together. But then they are all a bit sad, thinking about school the next day, and what that is going to change. They won’t have as much time to spend together, only able to come out here in the short window between school letting out and dinner, and then on the weekends. And, when it starts to get cold, they might not have anywhere they can sneak of to, as if the end of the summer really does mark the end of their magical haze.

But then this is interrupted as Andrea suddenly gets up, bolting to the bucket just in time to violently throw up, expelling everything that she has eaten that day, the boys gathering around her in concern as they try to comfort her. They have come to care for her quite a bit over the summer, seeing her as a lot more than just a shared girlfriend that they use for pleasure in exchange for getting to play in the tree house. None of them realize yet that this is the early sign of a very big memento of their summer.

**Author's Note:**

> If you're interested in my writing updates, please follow my fanfiction twitter @WattStalf  
> 


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